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Reiuued Apr. 8, 1952 zam rnooassroa rnonuoniff" IRA'LA rnorocnarmo rrrrAndre Emile Van Dormaeli heve'rlee liouvaiiiiand Laurent Aloys Van derAuwera, Mortsel- Antwerp, Belgium, assignors to Gevaertflhoto- ProductenN. V.,- Mortsel-Antwerp, Belgium, a

company ofBelgium No D awing original No. 2,529,890, dated Noyember '14,-l950,- erial No. 775,741, September- H l -2 3', 194 1. --A1 pli cation for reissue August u 1951, Serial No. 240,815. In Great Britain$epember 945?" J1 own. (or. 117-34) Matter enclosed in heavy bracketsappe ars in the original patent but forms no part of this reissuespecification; matter printed in italics indicates the additions ma'debyreissue.

Thisinven-tion relates to colored photographic layers, especially toanti-halationand filter ers and to the manufacture thereof. a

It is already known to prepare hernitricarlgoxl s-by.thetollevin l P-k;

lay-

wherein P -an organic group,

Q= an organic group,

or P and Q together= the non-metallic atoms necessary for completing acyclic basic nucleus,

Ar=an aryl group, 7

A=an atom of the 'chalcoge'n group. L

Hemitricarboxonoles containing an hydroxyl substituent in thepolymethine chain, however, are not known hitherto.

It is an object or the present" invention to provide a-new process forthe manufacture oi photographic layers, especially anti-halatiom Hand.filter layers.

FORMULA II HC--CH H Hl-CH C-(kni wherein P=an organic group such as CN,COOH, carbalkoxy, acyl,

Q-an organic group such as acyl, aryl, alkylamino, arylamino, hydroxyl,alkoxyl, carboxyl, carbalkoxy,

or P and Q together=the non-metallic atoms necessary. for. completing;.a nheterocvcli p111 cleus. occasionally... havinsa. fused-on arylene;

LQEIOUP. A anatom of the chaloogeugroup; y: This reactionfmay berepresented as iollows:

59 he re ti n nf 'l.,sa .llr i a acid d um- The starting productaccording to the above general formula (II) may be prepared with casefrom iuriurol; and a compqund with reactive me yl n mun; 1

according to the known' fnl 'cthods.

It is ible to add own anti-halationor filter dyestuils to the solutionused for coating on a new colored photographic layer. Said solution maybe incorporated in a colloid layer,. or to said'solution may be added acolloid hinder, or it may be' coated or spread without the assistance ofa colloid binder.

The following examples illustrate the invention more clearly. withoutlimiting, however, its scope.

Example 1 10 g. iuriurylidene-acetyl-acetic acid ethyl ester CHIprepared from iuriuroi and acetyl-acetic ethyl ester according to theparticulars given by Knoevenagel in Ber. 31 (1898) 734, dissolved in 100cm. .;of, ethyl alcohol, are treated with, 7 g. anthranili'caciddissolved in 90 cm'. ethylalcohol, and next with 14 g.methylene-disalicylic acid in 130 cm? ethyl alcohol.

After spreading this solution uponpthe rear surface of a photographicmaterial, an intense violet anti-halation layer with good covering powerand lacquer properties-is obtained. The probable formula is: n, V I L-.

i "1 on NHOH=CHCH=(!JOH=CC=O coon v fdgmooh- 6H. Examp1e2 g 13 g.furfurylidene-4-methyl-3-pheny1-l-pyrazolone-5.

He .o, cH;o-.- ,c =o

lilac-1 oam N preparedifrom furfurol and methyI-B-phe'nyl-I-pyrazoloneaccording to the instructions given by J. Tambor in Ber. 33(1900) 870, dissolvedin 250 cm. of ethyl alcohol, are treated with 5"g.aniline in,2 0 cm} ofethyl alcohol and .withll g. methylene-disalicylicacid in 140 cm.-'*. ethyl alcohol. After spreading thissolution upon therear surface of a photographic material, an intense blue anti-halationlayer with good coveringpower and lacquer properties is obtained.

The probable formula is;

6.5 g 'furfurylidene-4-methyl 3-phenyl lepy-.

razolone-5, dissolved in 150 cm? ethyl; alcohol, are treated with 3g.N-methyl-aniline in cm. alcohol and 7 g. methylene-disalicylic. acid incm. alcohol. After spreading this solution upon a glass plate, ananti-halation layer with- Example 4 2.4 g. furfurylidene-cyan-aceticacid anilide no-on ON Lake dissolved in cm. ethyl alcohol are treatedwith 4.2 g. piperidine in 50 cm. ethyl alcohol and 2.5 g.methylene-disalicylic acid in 100 cm. ethyl alcohol. After spreadingthis solution upon a glass plate, an intense red anti-halation layerwith good covering power and lacquer properties is obtained.

Probable formula according to Formula X cal-0H2 101v.

The furfurylidene-cyan-acetic acid anilide may be prepared byrefluxingcduring 15 minutes 8 g.

cyan acetic anilide in cm. ethyl alcohol and 5 g. furfurol. H

After cooling, the reaction product is recrystallized from ethylalcohol. Melting point: 178- 179 C.

We claim:

A process for the manufacture of an antihalation layer on a photographicglass plate, which comprises spreading upon, the glass plate a mixtureof furfurylidene-l-methyl-3-phenylrlpyrazolone-B dissolvedin alcohol,aniline in alco-- hol, and methylene-disalicylic acid in alcohol.LAURENT ALOYS VAN DER AUW ERA. ANDRE EMILE VAN DORMAEL.

REFERENCES CITED The following references are of record inthe file ofthis patentor the original patent:

v UNITED STATES PATENTS Number Name Date 1,631,421 Lohofer June 7, 19271,900,459 Moyse, Mar..7, 1,933 1,939,171 Hickman Dec. 12, 1933 2,158,287.Konig May 16. 1939 2,188,624 Brooker j Jan. 9, 19510 2,199,542 Konig.May 7, 1940 2,258,609 Hill Oct. 14, 1941 2,322,006

Fierke et 21. June 15,1913

